(E)-4-Chloro-2-[(4-hy-droxy-3-meth-oxy-benzyl-idene)amino]-phenol

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Schiff bases are versatile compounds with diverse applications.
• Vanillin derivatives are of interest due to their biological and chemical properties.

Purpose of the Study:

• To synthesize and characterize a novel Schiff base derived from vanillin.
• To investigate the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• The synthesis involved the reaction of 2-amino-4-chloro phenol with vanillin.

Main Results:

• The title compound, C14H12ClNO3, crystallizes with two conformationally distinct molecules in the asymmetric unit.
• Intramolecular hydrogen bonds (O-H⋯O, O-H⋯N) forming S(5) ring motifs were observed in both molecules.
• The extended crystal structure features a 3D network stabilized by O-H⋯O, C-H⋯Cl, C-H⋯O hydrogen bonds, and C-H⋯π/π-π interactions.

Conclusions:

• The study successfully synthesized and characterized a novel vanillin-derived Schiff base.
• The crystal structure reveals complex intermolecular interactions contributing to a 3D network.
• The findings provide insights into the structural diversity and supramolecular assembly of Schiff base compounds.